1,2-Epoxybutane → HCID 17943138, compound

HRID 609997Notes

Reaction equation

HRID 609997 reaction equation
[F:1][C:2]1[CH:16]=[CH:15][C:5]2[C:6]([CH:9]3[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]3)=[N:7][O:8][C:4]=2[CH:3]=1.[O:17]1[CH:19]([CH2:20][CH3:21])[CH2:18]1>C(O)(C)C>[F:1][C:2]1[CH:16]=[CH:15][C:5]2[C:6]([CH:9]3[CH2:10][CH2:11][N:12]([CH2:18][CH:19]([OH:17])[CH2:20][CH3:21])[CH2:13][CH2:14]3)=[N:7][O:8][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 78341,2-EpoxybutaneHCID 8494213-(4-Piperidyl)-6-fluoro-1,2-benzisoxazole

Product 1

HCID 17943138HCID 17943138, compoundYield 26.8%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
65 °C

Procedure

A stirred mixture of 4-(6-fluoro-1,2-benzisoxazol-3-yl)piperidine (5.5 g, 25 mmol) and 1,2-epoxybutane (1.89 g, 26.3 mmol) in isopropyl alcohol (100 ml) was heated at 65° C. for 2 days. This mixture was cooled and the solvent was removed to leave a brown oil which was purified by flash chromatography over a silica gel column (SiO2, 70 g; eluted with DCM, 1 l and MeOH:DCM 2%:98%) to give an off-white solid weighing 6.3 g. Recrystallization from hot ethanol yielded 1.96 g of fine crystals, m.p. 87-88° C.

Workup

  1. temperatureThis mixture was cooled
  2. customthe solvent was removed
  3. customto leave a brown oil which
  4. customwas purified by flash chromatography over a silica gel column (SiO2, 70 g; eluted with DCM, 1 l and MeOH:DCM 2%:98%)
  5. customto give an off-white solid
  6. customRecrystallization from hot ethanol

Sources & evidence

ORD record
ord-b2945e2a33834dc9a053ad14a865a95e
Source dataset
uspto-grants-1999_12
Patent number
US05998417

Reaction notes

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